Deciding whether to have a sidegig or quit your job? Here's the short (and long) answer.

"Should I quit my job to start my business?" I asked myself that question a lot back when I was gainfully employed.

Roughly five years ago, I quit a pretty solid job because I felt unfulfilled and wanted to build my own thing. I'd already teamed up with a group of people and we were excited to bring a cool concept to fruition. We had it mapped out, but that was about it. I quit, moved, and started up.

Six months later, I had little to no income and my savings were spent. I was living on credit cards, which (spoiler alert) is not a great financial decision.

The business was floundering. The stress, plus fundamental differences between founders, created a relational powder keg. When it blew up, it was almost comically bad.

A little under a year after leaving my job, I left my business. Next came an existential crisis. And that was on top of (literally) not being able to rub two nickels together at times. Oh, and then there was the looming debt. Fun times. It took me years to get back on my feet in a way that didn't require me to get a "normal" job again.

If I did it again, I would still go out on my own — no doubt about it. But I would do things differently. Since I learned the hard way, I thought I'd share a few pointers. And while I'm at it, I'll include some of what the internet and other indie hackers have said on the subject.

The options: Quit or (side) hustle

First off, you're not alone. According to a 2018 survey, 62% of Americans dream of one day becoming their own boss. I'd be surprised if that number isn't higher now. And with 41% of employees worldwide considering leaving their employers in 2021, I think a lot of people are wondering if they have what it takes.

If that's you, your options are pretty straightforward. Of course, you could stick with employment. Nothing wrong with that at all, but I think we can assume that most people in this community want something different. So that leaves taking the plunge and quitting right now, or keeping your job and starting a sidegig.

Should I quit my job to start my business or start my business to quit my job?

Let's assume that you've decided to quit your job. Then the question becomes, "When?" Should you quit your job to start up or start up to quit your job?

No easy answer here — it's a deeply personal and circumstance-dependent question. But let's lay out some basic pros and cons.

Quitting vs. sidegig: Pros and cons

Quitting will light a fire under you because you have no option but to succeed (or find a new job). It also frees up your time so that you can go all-in on your project and grow it faster.

But it also removes your salary, health insurance, 401k, and other benefits. This can be incredibly stressful, particularly as your money starts to dry up. And that, in turn, can lead to compromises, myopia, and diminished quality.

Sidegigs mean you can keep money in your pocket and avoid sacrificing your lifestyle. It also removes the risk, which means less stress.

But time becomes even more scarce, which is a different kind of stress. You'll have less time to work on your project and your limited availability may strain your relationships too.

So both options require sacrifice and some degree of stress. Ah, the joys of entrepreneurship.

Quitting vs. sidegig: Considerations

Ultimately, it'll depend on each person and their circumstances. Here are some factors that you may want to consider:

• Finances: This is the big one. What does it take to keep you afloat? How much do you have? How long will it have to last if you quit now? More on this below.
• Time: Speaking of resources, do you have the time for a sidegig? It's a lot like working two jobs.
• Responsibilities: This is related to time and finances — what are your responsibilities outside of your career? Parents and guardians, for example, may have a harder time deciding to take the plunge, and they may need more in the bank too.
• Business model: Your business model will have a big impact on the investment needed (both money and time), as well as how long it'll take to break even.
• Business stage: If you've already got your business going, or if you're thinking about buying one, then the stage of the business will have a big impact on your decision. The further along it is, the easier it'll be to make the jump.
• Urgency of quitting: Is your job unbearable? Is it an unhealthy work environment? These might be reasons to take the plunge sooner. Your mental and emotional well-being are important.
• Time-sensitivity of the idea: All ideas are time-sensitive, but some are more so than others. If it needs to happen now, that will impact your decision.
• Internal knowing: Many might disagree with this, but sometimes people just have an embodied hunch and they have to go for it. I'm all about following intuition.

While you mull this over, you may find it helpful to do a qualitative cost-benefit analysis — what will you sacrifice and what will you gain? There are some other good decision-making frameworks in this post, if it helps.

Tips for those who quit their jobs and start businesses

Get your finances in order

If you plan to quit your job, you'll need to make sure your finances are in order. Perhaps you have passive income or some freelancing opportunities. Or maybe someone has invested in your business or it's already profitable. But if not, you'll probably need a decent amount of savings.

You can calculate how much you'll need by figuring out how many months it'll take you to break even. Make sure to add a little cushion while you're at it, because things tend to take longer than expected. Then look at your bank statements and figure out how much you need in order to support yourself per month. Add some cushion there too. Then multiply them by each other and that's the minimum that you should set aside for your runway. From what I've seen most people recommend a minimum of 6 months savings. Most say a year. And I've even seen three years of savings. Here's a template for runway and cash budget planning that might help.

Validate it

If you're all set financially, make sure your business is ready for your undivided attention. Is it a great idea? Try to validate it before you quit. There are varying degrees of validation so you can choose methods according to how soon you need to quit. Check out my post on validation for more information.

Push the needle

In whatever time you have left before your last day, do everything you can to build (and spread the word about) your business. The further along it is, the better your chances.

Check in with loved ones

And, of course, if you have a significant other or someone who relies on you, have a conversation with them before putting in your notice.

Tips for those who keep their jobs and launch sidegigs

Make time

Just like those who decide to quit will need to take stock of their finances, you should probably take stock of your other resources if you opt for a sidegig. I'm talking about your time and energy, in particular. You'll probably need to put a lot of structure into your life. That means scheduling time for working on your sidegig outside of your day job — usually evenings and weekends. Here's a post on effective scheduling that might be helpful.

Stoke your motivation

To keep your motivation up on those long nights and weekends, try coworking groups like @charlierward's Weekend Club. Or check out this post on boosting your energy levels.

Take a vacation

Another idea I've seen a few indie hackers do is to take time off so that they can go all-in for a short time. Definitely worth considering.

Don't wait too long

And on the flipside of quitting too soon is wanting to quit but never doing it. Trust me, it happens all the time. So decide on a good time to quit, and stick to it. Maybe it's when you have $X saved, or when your side-gig is making $X/mo, or when you consider it validated, or maybe it's just a specific date. Set it and hold to it. Don't keep pushing it further and further away. At some point, you'll have to make the leap.

The short answer: Probably start a sidegig and quit your job later

The short answer is that it depends, but most founders that I've seen (myself included) would advise starting your business as a side-gig first, and working until you hit a specific goal. Usually that would be a certain amount saved or a certain degree of validation. Then go full-time on your project (or part-time along with some freelancing).

Here's what other indie hackers have to say on the topic — it's a varied response:

• @HelpStay said he burned his bridges before starting his business so that he had to commit — mind and spirit. He has never regretted that decision.
• @deppp advises getting your first paying customer before quitting.
• @jonathanbull validated EmailOctopus before leaving full-time employment. For him, validation meant paying base living expenses. It took two years, but meant that he had the runway to do it.
• @eruci quit before launching and it worked out, but he doesn't recommend it, as the first six months were tough and it was hard to focus while worrying about paying rent.
• @colaba suggests getting momentum going on a side project, saving up 6-12 months of runway, then quitting, and doing consulting if money runs short.
• @from_30_to_greatness took a paid vacation for a week to see what it was like to go full-time from a productivity standpoint. He says it was night and day, so he handed in his notice after one day of being back at work.
• Then there's @tayson who recently posted that a year after quitting and starting his business, he's made a total of $42. He notes that everything takes longer than you think, persistence is key, and launching is only the beginning. He's optimistic about the future.
• @levelsio recommends building a side project and quitting once the revenue of the project has surpassed your job for 6 months consistently. And have 3 years of savings. He also says it's going to be hard until you get traction. In his words, "You're entering a world of pain."

It's a difficult (but exciting) decision. Good luck! 🚀